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Family-friendly vacation rentals in Grosseto

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Grosseto family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars5 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favorite
Farm stay in Sovicille
5 out of 5 average rating, 23 reviews

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena

TimRating, 5 stars8 months ago
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place
Superhost
Home in Campo nell'Elba
4.9 out of 5 average rating, 145 reviews

Relax in the countryside near the sea( Lavanda )

LorianneRating, 5 stars4 months ago
Nous avons passé un super séjour en famille dans ce petit coin paisible au milieu de la nature ! Isabella est une excellente hôtesse! merci 😘 On recommande!!
Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 119 reviews

Villa a Montepulciano con Piscina

MichalRating, 5 stars5 months ago
Willa jest cudowna, duża i przestronna. położona w cichym miejscu z pięknym widokiem na winogronowe drzewa, góry Toskanii. Jeśli chcesz w pełni poczuć atmosferę pięknej Toskanii, ta willa jest idealnym wyborem. Byliśmy tam rodziną z trójką dzieci i dzieciaki nie chciały wyjść z basenu który był podgrzewany do godziny 18. Gospodarz był bardzo uprzejmy i pomocny. Dziękujęmy i już nie możemy się doczekać kiedy znów wrócimy !
Superhost
Home in Gaiole in Chianti
4.86 out of 5 average rating, 252 reviews

Charming estate with views

Deise Rating, 5 stars1 week ago
The best BandB we ever stayed. I am a very OCD person and I was very impressed how spotless and polish the place was. Everything was carefully thought out. Everything you need is in the place. Bernadino and His wife Luciana were amazing. Providing us with homemade Italian food and taxi services. They were so friendly that I am happy coming back with my kids. The view was breathtaking. Absolutely loved everything.
Top guest favorite
Cottage in Geggiano
4.99 out of 5 average rating, 127 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars2 months ago
Vila Di Geggiano was everything we were expecting it to be and more. We simply loved the place, quiet and very comfortable, set in the middle of a beautiful Toscana. The guest apartment is located by the side of the Main House, a historical summer palace with a deep history behind it. Andrea, our host, gave us a personal tour of the main house, filled with great stories about his ancestors. The house has been in Andrea´s family since the 1500s! If you are looking to spend some quiet days enjoying the great food and wine of Toscana in a relaxed, unique and comfortable space, Vila di Geggiano is a great destination for you.
Guest favorite
Cottage in Castell'Azzara
4.98 out of 5 average rating, 132 reviews

Your Private Tuscan Retreat

ShaunRating, 5 stars1 week ago
Our stay at Riccardo & Kate's property was fantastic, the property is as described, the views were awesome. Riccardo was more than happy to help us with local recommendations & bookings when we needed help as we speak next to no Italian. The local town of Castell'Azzara is a beautiful place & the local people were very helpful at the Coop, bakery & restaurants.
Guest favorite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

Michelangelo LiburdiRating, 5 stars4 months ago
se cercate un posto tranquillo e facile da raggiungere, è il posto ideale. proprietari disponibili ad ogni evenienza, appartamento corrispondente alla descrizione e super pulito. grazie Gaston per la gentilezza e disponibilità dimostrata, super consigliato

Family- and pet-friendly home rentals

Superhost
Apartment in Sasso Pisano
4.78 out of 5 average rating, 187 reviews

La Maison di Monica & Simona

MaximeRating, 5 stars3 months ago
Monica est très accueillante. Le rapport qualité prix est très correcte. Attention si vous avez des enfants en bas âge car il y a des escaliers un peu raide pour accéder au logement.
Guest favorite
Apartment in Marciana
4.79 out of 5 average rating, 100 reviews

Casa Piccola

KarinRating, 5 stars7 months ago
Die Wohnung haben wir sehr sauber und wie beschrieben angetroffen, und die Gastgeber waren sehr freundlich. Sie haben uns bei der Ankunft Tipps für Ausflüge gegeben. Anna Maria und ihr Mann haben hier ein kleines Paradies gestaltet. Wer Ruhe sucht, wird diese in dieser wunderschönen Umgebung auch finden. Die Terrasse ist nicht nur für Sonnenuntergänge perfekt, sondern auch für den Blick in den Sternenhimmel! Der Platz war für uns mit zwei Kindern ausreichend, da wir sowieso meist draussen waren. Den kleinen Laden im benachbarten Colle d'Orano können wir empfehlen. Wir haben die Woche in Patresi sehr genossen!
Superhost
Farm stay in Orbetello
4.64 out of 5 average rating, 115 reviews

Ground floor studio apartment in Farmhouse - pool

ValentinaRating, 5 stars2 weeks ago
Tutto bellissimo! Camera pulita e ben accessoriata la cucina con vista sul giardino e i campi maremmani. Ce ne siamo innamorate, consigliatissimo!
Top guest favorite
Condo in Cortona
4.98 out of 5 average rating, 129 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars1 month ago
We had an incredible stay at Clara's property in Cortona! The highlight of our trip was definitely the visit to the farm, which was not only fun but also deeply meaningful. We loved learning about the local way of life. Our host, Clara, was warm, welcoming, and extremely helpful throughout our stay. They went above and beyond to ensure we felt at home and had everything we needed. The property itself was clean, comfortable and well-located. We would highly recommend to anyone looking for an authentic and unforgettable experience in Cortona. Grazie mille, Clara for sharing your little slice of heaven with us!
Top guest favorite
Apartment in Montiano
4.98 out of 5 average rating, 44 reviews

Casa vacanza Poggio Bestiale

ChiaraRating, 5 stars7 months ago
L’alloggio è conforme alla descrizione e perfetto per una vacanza in assoluto relax. Posizione ottimale per raggiungere l’Argentario e nel contempo godere al rientro di un silenzio ed un panorama fantastico. L’appartamento è molto curato e pulito, Denise è un host superlativa, siamo stati molto molto soddisfatti.
Superhost
Apartment in Volterra
5 out of 5 average rating, 4 reviews

APPARTAMENTI 3 persone+ 4 persone

KasiaRating, 5 stars32 months ago
Claudia ist eine tolle Gastgeberin, immer sehr hilfsbereit und super nett. Wir haben uns sehr wohl gefühlt. Die Appartements haben alles was man braucht, das Pool ist super - sehr sauber und mit einem wunderbaren Blick. Die lage ist auch top - in etwa 15 Minuten ist man in der Volterra und bis zu San Gimignano braucht man nur eine halbe Stunde. Wir kommen sehr gerne wieder und bedanken uns für das leckere Öl und den schönen Urlaub!
Superhost
Farm stay in Montepulciano
4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars6 months ago
Le seul chose que je pourrais dire de négatif c’est le manque d’éclairage pour la cuisine et salle à manger . Pour le reste tout est parfait si on aime le décor de la campagne:-)
Top guest favorite
Condo in Asciano
5 out of 5 average rating, 166 reviews

Rosa come il cielo al tramonto

AjitRating, 5 stars1 week ago
We had a wonderful time at Lucia’s place . The house is charming and very clean . It is in the heart of beautiful Tuscany and you have exceptional view from every window . Checkin was easy and host is very kind and responsive . Highly recommended for a wonderful experience of Tuscany .

Family-friendly home rentals with a pool

Superhost
Apartment in Cortona
4.6 out of 5 average rating, 5 reviews

Medieval Cottage near Cortona

TommasoRating, 5 stars43 months ago
Un borgo meraviglioso immerso nel verde ma con tutte le comodità per trascorrere giornate all'insegna del relax e della tranquillità. Il borgo è stato ristrutturato in modo perfetto, lasciando intatto lo stile delle strutture. Gli appartamenti sono attrezzati con tutto il necessario e appena si mette piede fuori da casa si gode dei colori e dei suoni della natura, con la possibilità di fare anche un bel tuffo in piscina. Molto buono anche il ristorante e piacevolissima la compagnia dei cinghiali che si affacciano di tanto in tanto per un saluto. Davvero una bella scoperta!
Top guest favorite
Villa in Siena
4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

MarkRating, 5 stars6 months ago
We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!
Superhost
Apartment in Gaiole in Chianti
4.68 out of 5 average rating, 22 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars7 months ago
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!
Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft nel cuore del chianti toscano

CharlotteRating, 5 stars5 months ago
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.
Guest favorite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars5 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Superhost
Villa in Talla
4.91 out of 5 average rating, 22 reviews

Lovely villa heated outdoor pool & tennis court

LoriRating, 5 stars5 months ago
The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay
Guest favorite
Farm stay in Pienza
4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d'Orcia Pienza

RenatoRating, 5 stars4 months ago
host magnifici, ci hanno aiutato nelle richieste, sempre disponibili. la casa era come descritta e molto confortevole. Grazie
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars6 months ago
Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy

Quick stats about vacation rentals that are family-friendly in Grosseto

  • Total rentals

    40 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    480 reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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